Herringbone Digital Blog

A successful acquisition doesn’t end on closing day.In fact — that’s when the real work begins. The way you manage the transition period after a sale can determine whether the deal is remembered as a success or a slow-motion train wreck. Because here’s the truth: the ink may be dry, but your people, your clients, […]

I’ve been part of dozens of agency M&A deals — on both sides of the table. And if there’s one thing I’ve learned, it’s that seller’s remorse is real. Even when the money clears, even when the deal goes smoothly, many founders look back and say: “I wish I’d done a few things differently.” The […]

If you’ve never sold a business before, it’s easy to picture the finish line like this: you sign the papers, money hits your account, and you ride off into the sunset. Sometimes that’s true. But in most cases — especially in agency M&A — life after the sale is a transition, not a vacation. And […]

When people talk about selling their agency, the conversation almost always starts with numbers — valuation, multiples, EBITDA, earnouts. But here’s something I’ve learned after years of M&A work: the success or failure of most acquisitions isn’t determined by the financials. It’s determined by cultural fit. You can negotiate deal terms. You can structure earnouts. […]

Let’s talk about one of the most misunderstood (and emotionally charged) parts of any deal: negotiation. Most agency owners approach a negotiation thinking it’s all about one number — the price. But that’s exactly where most sellers go wrong. In reality, the purchase price is just one part of the deal. The structure — how […]

Few words in M&A trigger as much emotion as “earnout.” If you’ve ever talked to someone who sold their agency, chances are you’ve heard horror stories: “We never got our earnout.”“They changed the rules after closing.”“It was just a way to shortchange us.” And I get it. I’ve been on both sides of earnouts — […]

When most agency owners hear the words “due diligence,” their first thought is: “Oh no — this is where the fun ends.” And to be fair, diligence can be intense. It’s the part of the process where the buyer starts verifying everything you’ve told them — from your financials to your operations, contracts, people, and […]

If I could give agency owners just one metric to obsess over, it wouldn’t be revenue, it wouldn’t be headcount, and it wouldn’t even be profit. It would be client retention. Here’s why: I’ve seen it play out in real deals. Two agencies with the same $5M in revenue can command completely different valuations. One […]

Let’s be honest — most agency owners don’t start their business because they love bookkeeping. Numbers feel like a back-office chore, something you review once a year at tax time. But here’s the truth: to a buyer, your financials are the foundation of the business.  When a buyer looks at your numbers, they aren’t just […]

One of the first questions agency owners ask me is: “How do I know if I’m ready to sell?” It’s a fair question — but the answer isn’t always as simple as revenue or profit. Readiness is about much more than the numbers.Here are some of the key questions I encourage owners to ask themselves: […]